CN101225033B - Novel macrocyclic musk - Google Patents
Novel macrocyclic musk Download PDFInfo
- Publication number
- CN101225033B CN101225033B CN200810003325.XA CN200810003325A CN101225033B CN 101225033 B CN101225033 B CN 101225033B CN 200810003325 A CN200810003325 A CN 200810003325A CN 101225033 B CN101225033 B CN 101225033B
- Authority
- CN
- China
- Prior art keywords
- essence
- ketone
- joins
- compound
- encircles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is directed to novel compounds of the structure and a method for enhancing a perfume composition by incorporating an olfactory acceptable amount of the compounds provided as following.
Description
Invention field
The present invention relates to novel chemical substance, and this novel chemical substance is as introducing and the application of essence material.
Background of invention
In essence industry, in the urgent need to novel chemical substance is provided, make perfumer and other personnel can produce new fragrance for perfume, Gu Longshui and personal-care supplies.The difference that those skilled in the art will know that molecular structure of chemistry can cause the obvious different of smell, note (note) and characterization of molecules.These are different and make the perfumer use new compound to produce new fragrance to the needs of finding and use novel chemical substance to develop new fragrance.
Summary of the invention
The invention provides novel chemical substance, and use this chemical substance to strengthen the fragrance of perfume, toilet water, Gu Longshui, personal-care supplies etc.In addition, the present invention relates to use these new chemicals to strengthen the fragrance of perfume, toilet water, Gu Longshui, personal-care supplies etc.
More specifically, the present invention relates to the new compound that represents with following structural formula II and V:
But another embodiment of the invention is the method that strengthens flavor compositions (perfume composition) by the above-claimed cpd that adds the sense of smell receiving amount.
Add 7 of sense of smell receiving amount but the invention still further relates to a kind of passing through, 9-encircles 16 carbon diene-1-ketone and changes the method for essence preparation, and wherein said essence joins in the fabric care product.
But the invention still further relates to a kind of 7 of sense of smell receiving amount of passing through to add, 9-encircles 16 carbon diene-1-ketone and 8-encircles the method that cetene ketone changes the essence preparation, and wherein said essence joins in the fabric care product.
Can clearly understand these and other embodiment of the present invention by reading following explanation.
Detailed Description Of The Invention
Can then carry out elimination reaction according to following steps by making first corresponding olefin isomer (E/Z) carry out the alkene halogenating reaction, prepare compound of the present invention:
Raw material 8-ring cetene ketone (structural formula I) can be from (the Symrise GmbH of Si Muruisi company; Co.) buy, for above-mentioned reaction, reagent is purchased from A Deruiqi chemical company (Aldrich Chemical Company).8 of structural formula II I, 8 (9)-bromo-8-of 9-dibromo ring cetene ketone and structural formula IV ring cetene ketone is intermediate product, they do not separate and as roughage.Those skilled in the art will know that KOtBu represents potassium tert.-butoxide.
Those skilled in the art will know that compounds more of the present invention have a plurality of pairs of keys, thereby described compound have many geometrical isomers (EE, EZ, ZE or ZZ).In the present invention, described compound comprises the isomer mixture of these compounds, and can use technical point well known by persons skilled in the art from the isomer of these compounds.Suitable technology comprises chromatography, for example HPLC, particularly gel chromatography, and solid-phase microextraction (" SPME ").
The inventor has been found that the essence compound of structural formula II and V can give the essence preparation natural fragrance, is suitable as very much perfume ingredient.8-ring hexadecine ketone (V) has note like the gentle Moschus as Moschus odorant (odorant).7,9-encircles 16 carbon diene-1-ketone (II) and has note like gentleness, powdery, the Moschus.
According to an embodiment of the invention, the odorant that provides or aromatics (aromamixture) comprise 7,9-and encircle 16 carbon diene-1-ketone and 8-ring cetene ketone.7,9-encircles 16 carbon diene-1-ketone, and (7,9-cyclohexadecadien-1-one) weight ratio with 8-ring cetene ketone (8-cyclohexadecenone) is preferably 6: 1 to 1: 2, more preferably 4: 1 to 1: 1.
1: 1 mixture that 8-ring cetene ketone and 7,9-encircle 16 carbon diene-1-ketone has musky note shen strong, powdery.
Compound of the present invention can be widely used for present spice product, comprises preparation perfume and Gu Longshui, and the fragrance that increases personal-care supplies such as soap, body wash and hair care articles and air freshener and cosmetic products.The present invention also can be used for increasing the fragrance of sanitising agent, and described sanitising agent comprises but is not limited to washing composition, dishwasher detergent, scrubs composition, washes window agent etc.
In these goods, compound of the present invention can use separately, perhaps is used in combination with other flavor compositions, solvent, auxiliary agent etc.The character of spendable other component and kind are well known by persons skilled in the art.
Permitted eurypalynous essence (fragrance) and be can be used for the present invention, unique restriction be these essence should with other component compatibility of using.Suitable essence includes but not limited to: fruit, for example almond, apple, cherry, grape, pears, pineapple, orange, strawberry, raspberry; Moschus, fragrance of a flower agent, for example lavender like, rose like, iris like fragrance like, the carnation.The fragrance of other pleasant comprises from the draft of pine tree, dragon spruce and other forest smell and the smell of forest plants.Essence can also be from various oil, such as essential oil, or from vegetable material, such as Mentha arvensis L. syn.M.haplocalyxBrig, Mentha viridis L etc.
United States Patent (USP) the 4th, 534 provides a series of suitable essence No. 891, and the full content of this patent is by with reference to being incorporated into this.Other source of suitable essence is seen
Perfumes, Cosmetics andSoaps, second edition, W.A.Poucher compiles, and 1959.The essence that provides in this paper comprises hay, flores aurantii, orchid, Reseda odorata, sweet pea, trifolium, Tuberose, vanilla, violet, Flower of Common Wallflower of gum arabic, Acacia, chypre, Cyclamen persicum, fern, cape jasmine, hawthorn, Heliotrope, Japanese Honeysuckle, jacinthe, jasmine, cloves, lily, lily magnolia, Touch-me-notAction Plant, narcissus, fresh cutting etc.
The sense of smell significant quantity is interpreted as referring to the amount of compound in the flavor compositions, and each component is contributed its specific olfactory characteristic, but the aroma effect of flavor compositions is the general effect of each spices or perfume ingredient.Therefore, compound of the present invention can be used for regulating the fragrance characteristic of flavor compositions, perhaps regulates fragrance characteristic by the olfaction reaction that changes other component contribution in the flavor compositions.Described sense of smell significant quantity is with many factors vary, and these factors comprise other component, their relative quantity and required effect.
The content that is used for the compounds of this invention of aroma material preparation is about the 0.005-10 % by weight, preferably is about the 0.5-8 % by weight, is most preferably the 1-7 % by weight.Except described compound, other reagent can use with described essence.In the case without departing from the scope of the present invention, can also seal such as tensio-active agent, emulsifying agent, polymkeric substance with well-known material as described in essence.
The method of the content of the compounds of this invention is that compound makes flavor compositions have weight percentage shared in the material of required fragrance in adding in the another kind of expression flavor compositions.Compound of the present invention is about the 0.005-70 % by weight of described flavor compositions, preferably is about the 0.1-50 % by weight, is most preferably the 0.2-25 % by weight.Those skilled in the art can use the compounds of this invention of desired content that required fragrance and intensity is provided.
Following examples provide as the specific embodiment of the present invention.Those skilled in the art understand other mode of ameliorating of the present invention easily apparently.These improvement are understood to include within the scope of the invention.Unless indication is arranged in addition, all used in literary composition percentage ratios are weight percentage, and ppm is interpreted as representing umber/1,000,000, and g is interpreted as gram.The IFF that uses among the embodiment is interpreted as referring to (the International Flavors ﹠amp of International Perfume ﹠ Essence Co. in New York, United States New York; Fragrances Inc., New York, NY, USA).
Example I
7,9-encircles the preparation of 16 carbon diene-1-ketone (II)
In reaction flask, add 8-ring cetene ketone (236 grams, 1 mole), sodium acetate (10 grams, 0.1 mole) and methylene dichloride (500 milliliters).Make solution be cooled to 10 ℃, then in 2 hours, add bromine (240 gram).Make reactant be warmed up to room temperature, with 500 milliliters of saturated aqueous sodium carbonate washings.By the rotary evaporation desolventizing, obtain rough 8,9-dibromo Cyclohexadecanone (III).
150 ℃ with rough 8,9-dibromo Cyclohexadecanone joins in the reaction vessel of the slurry that contains 700 milliliters of dimethyl formamides (DMF) and Quilonum Retard (111 grams, 1.5 moles).Reactant was worn out 14 hours.Use first 2 premium on currency, then use 10% acetic acid aqueous solution (500 milliliters) washing reaction.(2%NaOH) distills with caustic soda, obtains 54 grams, 7,9-and encircles the mixture that 16 carbon diene-1-ketone and 86 gram 8-ring cetene ketone and 7,9-encircle 16 carbon diene-1-ketone.
7,9-encircles the analytical data of 16 carbon diene-1-ketone:
Boiling point 166-168 under 3 mmhg ℃.
H
1NMR data: 1.19-1.44ppm (m, 9H), 1.49-1.85ppm (m, 5H), 1.98-2.24ppm (m, 4H), 2.27-2.56ppm (m, 4H), 5.17-6.37ppm (m, 4H).
7,9-encircles the odor characteristics of 16 carbon diene-1-ketone: note like the gentle powdery Moschus.
8-ring cetene ketone and 7,9-encircle the odor characteristics of 1: 1 mixture of 16 carbon diene-1-ketone: note like the strong powdery Moschus.
Example II
The preparation of 8-ring hexadecine ketone (V)
With rough 8 by the preparation of 8-ring cetene ketone in the above-described embodiments, 9-dibromo ring cetene ketone joins in the reaction vessel that contains dimethylbenzene (1 liter), the trimethyl carbinol (1 liter) and potassium tert.-butoxide (280 restrain 2.5 moles).This reaction is heated to backflow, aging 6 hours.Acetic acid aqueous solution with 10% (500 milliliters) cancellation reaction.With the crude product flash distillation, obtain containing the mixture of 8-ring hexadecine ketone, 8-bromine ring 16 carbon-8-ketenes and 8-ring cetene ketone.Fractionation obtains 35 gram 8-ring hexadecine ketone.
The analytical data of 8-ring hexadecine ketone:
Boiling point under 2 mmhg is 153 ℃
H
1NMR data: 1.28-1.39ppm (m, 10H), 1.41-1.52ppm (m, 8H), 1.60-1.73ppm (m, 4H), 2.17-2.23ppm (m, 4H), 2.40ppm (t, 2H, J=2Hz), 2.46ppm (t, 2H, J=2Hz).
The odor characteristics of 8-ring hexadecine ketone: note like gentle, the Moschus.
Embodiment 3
Essence preparation: sweet/flower infant powder agreement (sweet/floral baby powder accord).
Santaliff
 |
2.4 part |
Phenoxanol
 |
3.2 part |
| Tonka bean camphor (Coumarin) | 2.8 part |
| High-quality α-methyl-p-isopropyl phenylpropyl aldehyde (Cyclamal Extra) | 0.1 part |
| Vanillal (Eth Vanillin) | 0.7 part |
| Geraniol 980 pure (Geraniol 980 Pure) | 0.1 part |
| Hedione | 6.0 part |
| Amyl cinnamic aldehyde (Amy Cinnamic Aldehyde) | 6.0 part |
| Heliotropine (Heliotropine) | 1.7 part |
| Hexyl cinnamic aldehyde (Hexyl Cinnamic Ald) | 1.6 part |
| High-quality alpha, beta-lonone (Beta Ionone Extra) | 0.6 part |
Iso?E?Super
 |
7.0 part |
Lyral
 |
1.6 part |
lillial
 |
16.0 part |
| Lilianth | 2.0 part |
| Methylionone γ A (Methyl Ionone Gamma A) | 7.3 part |
| Veramoss (Veramoss) | 0.2 part |
| Peru balsam oil (Peru Balsam Oil India) | 0.3 part |
| Acetic acid isoprene ester (Prenyl Acetate) | 0.1 part |
| Vertofix coeur (Methyl Cedryl Ketone) | 4.0 part |
| Methyl phenylacetate (Methyl Phenyl Acetate) | 0.1 part |
| Aubepine (Aubepine) | 0.4 part |
| Bitter almond oil camphor (Benzoin) | 1.0 part |
| Cypress camphor (Cedrol) Tex | 0.3 part |
| High-quality geraniol (Citronellol Extra) | 0.3 part |
| Geraniol (Geraniol) Coeur | 0.4 part |
| Methyl cinnamate (Methyl Cinnamate) | 0.3 part |
| Styrax?Alva?Ess | 0.2 part |
| Vanillin?ex?Lignin | 1.2 part |
| Java this real estate cananga oil (Cananga Java Native) | 0.5 part |
[0040]?
| Described article | 6.6 part |
The mixture that encircles 16 carbon diene-1-ketone and 8-ring cetene ketone (1: 1 weight equivalent) with 7,9-prepares above-mentioned essence.With respect to containing Globanone
TMThe preparation of (substituting said mixture) carries out smell relatively.The evaluation of two kinds of essence shows that 7,9-encircles 16 carbon diene-1-ketone and 8-ring cetene ketone essence ratio contains Globanone
TMThe smell of essence stronger.
Claims (27)
1.7 9-encircles 16 carbon diene-1-ketone.
2. but method that changes the essence preparation by the compound as claimed in claim 1 that adds the sense of smell receiving amount.
3. but method that improves the essence preparation by the compound as claimed in claim 1 that adds the sense of smell receiving amount.
4. method as claimed in claim 2 is characterized in that, described essence joins and is selected from the following product: perfume, cosmetic products and fabric care product.
5. method as claimed in claim 2 is characterized in that, described essence joins and is selected from the following product: Gu Longshui and toilet water.
6. method as claimed in claim 2 is characterized in that, described essence joins in the air freshener.
7. method as claimed in claim 2 is characterized in that, described essence joins among the personal care product.
8. method as claimed in claim 2 is characterized in that, described essence joins in the cleaning product.
9. such as each described method among the claim 4-8, it is characterized in that the amount that joins the described compound of claim 1 in the essence is the 0.005-10 % by weight.
10. such as each described method among the claim 4-8, it is characterized in that the amount that joins the described compound of claim 1 in the essence is the 0.5-8 % by weight.
11., it is characterized in that the amount that joins the described compound of claim 1 in the essence is the 1-7 % by weight such as each described method among the claim 4-8.
12. an essence preparation, it contains the compound as claimed in claim 1 of sense of smell significant quantity.
13. an essence product, it contains compound as claimed in claim 1.
14. an odorant or aromatics, it comprises 7,9-and encircles 16 carbon diene-1-ketone and 8-ring cetene ketone.
15. odorant as claimed in claim 14 or aromatics is characterized in that, the weight ratio that 7,9-encircles 16 carbon diene-1-ketone and 8-ring cetene ketone is 6: 1 to 1: 2.
16. odorant as claimed in claim 14 or aromatics is characterized in that, the weight ratio that 7,9-encircles 16 carbon diene-1-ketone and 8-ring cetene ketone is 4: 1 to 1: 1.
But 17. one kind by adding 7 of sense of smell receiving amount, 9-encircles the method that 16 carbon diene-1-ketone and 8-ring cetene ketone change the essence preparation.
But 18. one kind by adding 7 of sense of smell receiving amount, 9-encircles the method that 16 carbon diene-1-ketone and 8-ring cetene ketone improve the essence preparation.
19. method as claimed in claim 17 is characterized in that, described essence joins and is selected from the following product: perfume, cosmetic products, fabric care product.
20. method as claimed in claim 17 is characterized in that, described essence joins and is selected from the following product: Gu Longshui and toilet water.
21. method as claimed in claim 17 is characterized in that, described essence joins in the air freshener.
22. method as claimed in claim 17 is characterized in that, described essence joins among the personal care product.
23. method as claimed in claim 17 is characterized in that, described essence joins in the cleaning product.
24., it is characterized in that the amount that joins the described compound of claim 1 in the essence is the 0.005-10 % by weight such as each described method among the claim 19-23.
25., it is characterized in that the amount that joins the described compound of claim 1 in the essence is the 0.5-8 % by weight such as each described method among the claim 19-23.
26., it is characterized in that the amount that joins the described compound of claim 1 in the essence is the 1-7 % by weight such as each described method among the claim 19-23.
27. method as claimed in claim 17 is characterized in that, the weight ratio that 7,9-encircles 16 carbon diene-1-ketone and 8-ring cetene ketone is 1: 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/623,425 US7838487B2 (en) | 2007-01-16 | 2007-01-16 | Macrocyclic musk |
| US11/623,425 | 2007-01-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101225033A CN101225033A (en) | 2008-07-23 |
| CN101225033B true CN101225033B (en) | 2013-05-29 |
Family
ID=39414934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810003325.XA Expired - Fee Related CN101225033B (en) | 2007-01-16 | 2008-01-16 | Novel macrocyclic musk |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US7838487B2 (en) |
| EP (1) | EP1947078B1 (en) |
| CN (1) | CN101225033B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6200254B1 (en) * | 1999-05-21 | 2001-03-13 | Takasago International Corporation | Macrocyclic ketones as fragrance materials and methods for making same |
| US20030049213A1 (en) * | 2001-06-08 | 2003-03-13 | Hiroyuki Matsuda | Melanin production inhibitors and skincare products containing such inhibitors |
| CN1874749A (en) * | 2003-11-04 | 2006-12-06 | 宝洁公司 | Fragrances comprising residual accords |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5531085A (en) | 1979-08-22 | 1980-03-05 | Takasago Corp | Preparation of cyclohexadeca-5,9,13-trien-1-one |
| FR2758138B1 (en) * | 1997-01-06 | 1999-01-29 | Rhodia Chimie Sa | PROCESS FOR REDUCING A CARBONYL COMPOUND |
| DE10038021A1 (en) * | 2000-08-04 | 2002-02-14 | Haarmann & Reimer Gmbh | New macrocyclic ketones |
| DE102005003338A1 (en) | 2005-01-25 | 2006-07-27 | Symrise Gmbh & Co. Kg | Preparation of 2-oxo-cyclo-alkane/alkene carboxylic acid ethylesters, useful as intermediate products to prepare macrocyclic ketones, comprises reacting diazoacetic acid ethylester with cyclo-alkanone/alkenone in the presence of Lewis acid |
-
2007
- 2007-01-16 US US11/623,425 patent/US7838487B2/en not_active Expired - Fee Related
-
2008
- 2008-01-11 EP EP08250151A patent/EP1947078B1/en not_active Not-in-force
- 2008-01-16 CN CN200810003325.XA patent/CN101225033B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6200254B1 (en) * | 1999-05-21 | 2001-03-13 | Takasago International Corporation | Macrocyclic ketones as fragrance materials and methods for making same |
| US20030049213A1 (en) * | 2001-06-08 | 2003-03-13 | Hiroyuki Matsuda | Melanin production inhibitors and skincare products containing such inhibitors |
| CN1874749A (en) * | 2003-11-04 | 2006-12-06 | 宝洁公司 | Fragrances comprising residual accords |
Non-Patent Citations (1)
| Title |
|---|
| A. J. HUBERT.1240.Macrocyclic Compounds.Part XI.1 A Novel Synthesis of Civetone Hornologues..《Journal of the Chemical Society》.1965,6679-6681. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1947078A1 (en) | 2008-07-23 |
| US7838487B2 (en) | 2010-11-23 |
| EP1947078B1 (en) | 2011-10-26 |
| CN101225033A (en) | 2008-07-23 |
| US20080171796A1 (en) | 2008-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3279300B1 (en) | Fragrance composition | |
| CN102858930B (en) | Organic carbonates with vanilla odor | |
| CN102802600B (en) | As 2,4-disubstituted pyridines of perfuming component | |
| ES2400841T3 (en) | Novel 4-alkylcyclohexanopropanal compounds and their use in perfume compositions | |
| EP3072877A1 (en) | Ester | |
| CN113025426A (en) | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient | |
| CN101580468A (en) | Optically active ester compounds and application in perfume compositions | |
| EP2904076B1 (en) | Flavor and fragrance formulation (iii) | |
| US4671798A (en) | 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-1-naphthalenol, its use as perfuming ingredient and process for making same | |
| CN104003882A (en) | Novel organoleptic compound | |
| EP2804579B1 (en) | Novel organoleptic compounds | |
| CN101225033B (en) | Novel macrocyclic musk | |
| EP1790630B1 (en) | Derivatives of 3-cyclopropyl-1-propanone compounds and their use in perfume compositions | |
| CN100374432C (en) | Acetonide fragrance compound | |
| EP3730476B1 (en) | Compound having musk-like scent and perfume composition containing same | |
| CN108290812A (en) | Novel octahydro indenyl propionic aldehyde compound | |
| JPH01289898A (en) | Method for intensifying, improving or modifying odor characteristics of compound perfume or scented product, compound perfume and scented product having intensified, improved or modified odor characteristics, and method for preparing 2-methoxy- 4-propyl-1-cyclohexanol | |
| CN102227418B (en) | Acetals as perfuming ingredients | |
| US4912088A (en) | Use of campholenenitriles as fragrance | |
| CN103649035A (en) | Musk odorant with aromatic notes | |
| CN103717723B (en) | Violet leaf flavoring agent | |
| CN104837798B (en) | Sage odorant | |
| CN103370296A (en) | Perfuming ingredient of the galbanum family | |
| CN108203622A (en) | Novel sensory compounds | |
| EP0456932A1 (en) | Propanol derivatives and perfumes containing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130529 Termination date: 20160116 |
|
| EXPY | Termination of patent right or utility model |